Well, brokenentity (the Skeezyks says with a sour expression on his wrinkled old face) there's one very crass joke I can't tell here that applies in these situations. There's also the old saying (I think Ben Franklin may have said it): "neither a borrower nor a lender be." There's probably a number of other pithy sayings one could apply here. I can't happen to think of them right at the moment... (senior dementia...)

I know you want to be a good person. And I believe you are. But, my personal opinion is: never lend money to anyone! If you want, & can afford to, give to reputable charities. There are more needs in this world than any one of us can ever even begin to address. So, whatever your interest, give to charities that address those particular needs. You might even give money to a friend, who has a particular need. But give it under the assumption it is a gift, not a loan.

From my perspective, I think what you have to ask yourself is what is causing you to do what you're doing? Are you trying to "buy" friendship & respect? Are you so down on yourself you feel you must do these kinds of things in order to fill a void that exists inside of you? Certainly friendship, respect & love are necessary. But so are boundaries. And each of us has to set our own. It's sounding to me as though you may not have any, or at least not ones that are sufficient. And the problem with this is, if you continue down this path, these sorts of things will continue to occur. You don't want that, I don't believe.